I recently posed this question to my colleague Steven Samra. He’s worked in street outreach with veterans in Nashville, Tennessee, and brings his own personal journey through addiction and homelessness to this work.

For three months, Steven had been spending time getting to know people at Library Park in Nashville. Over the years, the park has become decidedly unfriendly towards people experiencing homelessness. But several years ago it was perhaps the most popular spot in the downtown area for those experiencing homelessness to congregate due to its proximity to shelter and restroom access at the nearby library.

During this time, Steven met David (not his real name). As a result of gross obesity, diabetes, and additional chronic health problems, David was essentially anchored to a bench within the park. Over the period of several months, Steve slowly engaged David in conversation. Initially, they spoke just a few words, or shared the three minutes of time it takes to smoke a cigarette. As time passed, conversations grew longer and became more intimate, as Steven listened to David share his story. It was also at this point that David shared his real name with Steven, who had known him only by his street name, “Bones.”

One day, David approached Steven and said, “I have been watching you for three months. I definitely need to get some housing, but I am going to tell you that you have three strikes to find me housing. If you can’t get it together by then, you can ‘kick rocks’ because I’m tired of flash in the pan, pie in the sky promises by people who say they can help me.”

In one sentence, David shifted Steven’s concept of outreach by one hundred and eighty degrees. “He needed the help, yet he was setting the conditions,” says Steven. I smiled, knowing what Steven would tell me next. Steven saw this as a challenge. He recognized the beauty of what he understood was an empowering place for a man who had lost so much over the course of his life.

At that moment, the two men began to work together.

The next weekend, Steven and David had an appointment with an affordable housing program for 11 am. Steven picked David up in his car at 10:50 and when they arrived just two minutes after 11, they were told they missed the appointment and would have to return to fill out the application. “I was so mad I could barely contain my anger. I knew the person we were supposed to be seeing that day wasn’t there. I began to think how frustrating and demeaning it would be for David, or anyone seeking a home, to face such an unwelcoming bureaucracy on his own.”

“In that moment, I understood why remaining on the park bench would be an option. I understood why the people we encounter on the street are often hopeless, disillusioned, despondent, and cynical,” says Steven. This incident provided insight into the difficulties of facing a system that exerts control over people in dire need of care. And it fueled Steven’s determination to find housing for David as quickly as he could.

“I became an absolute champion for housing, and for the people who are seeking it. That was the defining moment. Even when I was a child, moving from school to school as my parents tried to remain employed, I have always stood up for the underdogs, for people who, for whatever reason, weren’t in a position to defend themselves. When this happened to David, “that was it, the gloves were off, and it was on,” says Steven.

Eleven months later David had housing, a social security income, had entered into recovery, and received medical care. Today, David has reconciled relationships with his son and grandson, has been clean, sober, and housed for two years. His health has improved considerably and he remains relatively stable. David now speaks to others about his experiences. The two men remain in touch.

“David is a wonderful guy. He’s as hard core blunt and honest a man as you will ever meet, but he was willing to stand up for himself and say ‘I’m tired of people telling me how I am going to do things.’” Steven says the lessons he learned with David still help shape his approach to the work. He warns others not to grab the tiger by the tail. “You can push a person just so far before they begin to push back. If we’re making demands on people experiencing homelessness, we ought to make certain we’re able to fulfill their requests when they meet our demands.

What about you – what has been a defining moment in your career in homeless services?